Cheapest return flights from Chicago to San Juan in December from 212€

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in December 2025 (see full year).

Return flights

05 Dec - 10 Dec Frontier Airlines
05 Dec - 14 Dec Southwest Airlines
06 Dec - 09 Dec Southwest Airlines
06 Dec - 14 Dec Southwest Airlines
05 Dec - 07 Dec Southwest Airlines
04 Dec - 08 Dec Frontier Airlines
03 Dec - 07 Dec Southwest Airlines
24 Dec - 30 Dec Frontier Airlines
15 Dec - 22 Dec Southwest Airlines
04 Dec - 07 Dec Southwest Airlines
29 Dec - 09 Jan Frontier Airlines
24 Dec - 10 Jan Frontier Airlines
30 Dec - 04 Jan Frontier Airlines
21 Dec - 06 Jan Frontier Airlines
30 Dec - 02 Jan Frontier Airlines
28 Dec - 06 Jan Frontier Airlines
30 Dec - 03 Jan Frontier Airlines
29 Dec - 03 Jan Frontier Airlines
23 Dec - 02 Jan Frontier Airlines
26 Dec - 03 Jan Frontier Airlines

Also check the deals for one-way flights from Chicago to San Juan in December.

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